Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane
The total synthesis of (–)-γ-lycorane (10 steps) and synthesis of (±)- γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* deprotection/cyclisation procedure was developed for de novo formation of the fused...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Royal Society of Chemistry
2022
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| _version_ | 1826307916743835648 |
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| author | Hall, C Marriott, I Christensen, K Day, A Goundry, W Donohoe, TJ |
| author_facet | Hall, C Marriott, I Christensen, K Day, A Goundry, W Donohoe, TJ |
| author_sort | Hall, C |
| collection | OXFORD |
| description | The total synthesis of (–)-γ-lycorane (10 steps) and synthesis of (±)-
γ-lycorane (8 steps) was completed from cyclohexenone. A new
two step hydrogen borrowing alkylation of an aziridinyl alcohol,
coupled with a Ph* deprotection/cyclisation procedure was
developed for de novo formation of the fused 6,5 heterocyclic ring.
This work is one of the first examples of hydrogen borrowing C-C
bond formation being used as a key step in a total synthesis project. |
| first_indexed | 2024-03-07T07:10:14Z |
| format | Journal article |
| id | oxford-uuid:10812176-ca41-4f1e-b1c1-25709e457018 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:10:14Z |
| publishDate | 2022 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:10812176-ca41-4f1e-b1c1-25709e4570182022-06-22T08:39:15ZExtension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycoraneJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:10812176-ca41-4f1e-b1c1-25709e457018EnglishSymplectic ElementsRoyal Society of Chemistry2022Hall, CMarriott, IChristensen, KDay, AGoundry, WDonohoe, TJThe total synthesis of (–)-γ-lycorane (10 steps) and synthesis of (±)- γ-lycorane (8 steps) was completed from cyclohexenone. A new two step hydrogen borrowing alkylation of an aziridinyl alcohol, coupled with a Ph* deprotection/cyclisation procedure was developed for de novo formation of the fused 6,5 heterocyclic ring. This work is one of the first examples of hydrogen borrowing C-C bond formation being used as a key step in a total synthesis project. |
| spellingShingle | Hall, C Marriott, I Christensen, K Day, A Goundry, W Donohoe, TJ Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title | Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title_full | Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title_fullStr | Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title_full_unstemmed | Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title_short | Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane |
| title_sort | extension of hydrogen borrowing alkylation reactions for the total synthesis of γ lycorane |
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